I'm not sure "looks" matter THAT much.
I think BY FAR the biggest reason this domain will underperform is simply because of the simple maths of it.
Specifically the number of buyers has diminished since the new owner purchased it.
If this domain was bought at auction and he was the highest bidder, then that means the person willing to pay the most is now the second highest bidder, given that new owner is now no longer bidding and the past owner is unlikely to buy it is he just sold it.
So the idea you can buy a domain at auction, then sell it the next day on the same auction platform is flawed because the actual number of buyers has reduced.
From my perspective the "inherent value" of domains hasn't really changed over the last 5 - 7 years, the only thing that has changed is the "number" of buyers that recognise the value and who are willing to buy them which is what is forcing prices up over time.
And the only reason why domain prices will go higher from here is if even more businesses become aware of the value of domain names.